Billy Libby is the co-founder of Upper90, a firm that invests in a hybrid of debt and equity in early-stage technology companies to help founders scale efficiently. Billy partnered with Jason Finger, the founder of Seamless, to address a capital structure inefficiency in the venture world. Upper90 has deployed $1 billion of capital for an LP base of more than 300 entrepreneurs.

Our conversation covers Billy’s background in electronic trading, formation of an investment club that brought together quantitative investors and tech founders, and the evolution of that club into Upper90. We discuss Upper90’s approach to investing in tech start-ups, use of data to find lendable opportunities, sourcing and diligence of deals, and lots of examples along the way.